Make a Confident Impression. 5 Simple First Date Outfits

first date outfit


What is it about a first date that makes the most confident woman a slightly nervous wreck?

Are you going to like him? Is he going to like you? What were you thinking agreeing to meet a stranger for lunch!

Talk about being outside your comfort zone. Whether you’ve been fixed up on a blind date by a friend or met online, meeting someone new for the first time never feels as easy as we’d like it too.

I don’t care if you’re Jennifer Lopez and looking at marriage number four. Your outer shell projects confidence and sass with the hope this date will not be a huge waste of time. Your inner girl is a little more fragile. Maybe his name is the same as your ex’s. He may sound like a great guy but you never know until you lock eyes. Maybe he likes big boobs and you’re not a big boob.

The only way to go into a first date is with confidence, reasonable expectations and looking like you couldn’t give a damn. You’re going to be so comfortable and pulled together, he won’t know what hit him. Even if he’s not the one, especially if he is the one, you’ll want to feel in control of your game. When we look good, we feel good. That my love is how we get through life and first dates.

Your mission is to become a stealth bomber. Does the bomb care where it goes or who it hits? Heck no. It just IS the bomb. And that’s enough. We’re not saying you’re a destroyer; just own what you are. Don’t make apologies or excuses. Just be the bomb.

Hair, makeup. Check. I wouldn’t say go overboard. You know by now what looks good on you. Don’t try to cover up your natural beauty with a ton of lashes or perfume. Honey that will only catch the wrong ones. Subtle, don’t give a damn makeup is your goal.

Ditto with your hair. Now I happen to think hair is a pretty big deal. Am I right? You know what to do.

Now we’re at the good stuff. What to wear on a first date.

I’m a very visual person. If you were in front of me I’d know exactly what you’d look good in and what would flatter you. But through the magic of the internet, we’re going to set you up with some dude-slaying outfits, five altogether. I know one of them is going to fit you to a T.

I believe the most powerful first date outfit a woman can wear is a dress. Not too slutty, not too night-time but just the right amount of “I know I’m the bomb”.

First Date Outfits

Shirt Dress

Maxi Dress

Tank Shift Dress

Fit & Flare Dress

Shift Dress

Just remember, clothes do make a difference. But it’s your inner confidence that’s going to make this first date bearable, survivable and hopefully a hoot. Honey… take that “I am the bomb” attitude with you and you’ll be just fine.




I created Hip Over Fifty for all the women who want to stay hip and relevant in their fifties and beyond. Staying connected and encouraging each other is what inspires me. I hope to hear your thoughts and dreams too!

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